Synthesis and Self-Assembly of Bolaamphiphiles Based on β-Amino Acids or an Alcohol

The synthesis of bolaamphiphiles from unusual beta-amino acids or an alcohol and C12 or C20 spacers is described. Unusual beta-amino acids such as a sugar amino acid, an AZT-derived amino acid, a norbornene amino acid, and an AZT-derived amino alcohol were coupled with spacers under standard conditions to get the novel bolaamphiphiles 58 (Scheme 1), 12 and 13 (Scheme 2), and 17 and 20 (Scheme 3). Some of these compounds, on precipitation from MeOH/H2O, self-assembled into organized molecular structures.